What to expect on your Tuscany walking holiday
Four Guided Walks
Walk through iconic Tuscan landscapes following sections of the Via Francigena

San Gimignano
Stay in the heart of Tuscany, surrounded by spectacular views across the Tuscan countryside

Wine Tasting
Enjoy wine tasting at Castello di Volpaia a historic wine estate in the heart of the Chianti Classico region

Medieval Hilltop Towns
Visit beautiful historic towns including Radda in Chianti, Monteriggioni and Asciano
About this trip...
Return transfers (these transfers are time specific)
Private room for sole use
Breakfast daily, 1 lunch & 2 dinners
Gelato tasting
Wine tasting
Welcome drink & information meeting
4 guided walks
Free Solos App with all your travel documents
Dedicated WhatsApp group for your trip
Accompanying Solos Tour Leader
- Domestic and or International flights are not included
- Let us help you book them! Learn more.
- Private Airport transfers
- Travel insurance
- Tips & drinks
- Meals when not included in the itinerary
- Activities when not included in the itinerary
- Tourist Tax €3.00 per night (payable locally)
What you'll be doing

Day One: Arrival Day
- Dinner included

Day Two: San Gimignano Loop
- Distance: 8km/5 miles
- Duration: 3-4hrs approx.
- Ascent: 215m+/705ft+
- Terrain: A mixture of quiet country lanes, unpaved tracks and well-established trails, with some uneven and gently undulating sections. Expect a few moderate climbs and descents through vineyards, olive groves and rolling Tuscan countryside.
- Breakfast & lunch included

Day Three: Radda to Volpaia
After breakfast, we depart for the charming hilltop village of Radda in Chianti. From here we'll walk through the spectacular landscapes of the Chianti Classico region towards the medieval village of Volpaia. The route follows quiet gravel tracks and country paths through rolling vineyards, olive groves and shady woodland, with beautiful panoramic views across the surrounding Tuscan hills. Along the way, pass historic farmhouses and traditional Chianti vineyards before the route climbs gently towards Volpaia, where the ancient fortified village and its castle provide a wonderful reward at the end of the walk.
- Transfer Time: 1hr + 1hr
- Distance: 6km/3.7 miles
- Duration: 2-3hrs approx.
- Ascent: 215m+/705ft+
- Terrain: A mix of paved paths, quiet roads, and well-maintained woodland trails, with some uneven ground, gentle inclines, and steps.
- Breakfast included

Day Four: At Leisure
Today is ours to enjoy San Gimignano at our own pace. Explore its atmospheric medieval streets and historic towers, browse the local shops and cafés, or simply relax and soak up the beautiful Tuscan surroundings.
- Breakfast included

Day Five: Strove to Monteriggioni
After breakfast, we’ll travel by bus to the charming village of Strove, where we’ll begin our walk through the peaceful Tuscan countryside towards the medieval walled village of Monteriggioni. Following quiet country lanes and rural tracks, the route winds through the rolling landscapes of the Val d’Elsa, passing vineyards, olive groves and woodland along the way. We’ll also visit the atmospheric village of Abbadia a Isola, with its historic abbey, before continuing through the beautiful countryside to Monteriggioni, one of Tuscany’s best-preserved medieval fortified villages.
- Transfer Time: 30mins + 35mins
- Distance: 6.5km/4 miles
- Duration: 2-3hrs approx.
- Ascent: 100m+/328ft+
- Terrain: A mixture of quiet country lanes, gravel tracks and rural paths, with generally gentle, rolling terrain. Expect some uneven and unpaved sections as the trail passes through vineyards, olive groves and woodland, with a few gentle climbs and descents along the way.
- Breakfast included

Day Six: Asciano Loop
Today we depart for the historic town of Asciano to explore the beautiful Crete Senesi, one of Tuscany’s most distinctive landscapes, on a scenic circular walk. Our route passes through the rolling countryside, characterised by gently undulating hills, cultivated fields and classic Tuscan scenery, before visiting Asciano, a charming medieval town rich in history and character. We’ll also visit the magnificent Abbazia di Monte Oliveto Maggiore, a peaceful Benedictine monastery set amid woodland and countryside, renowned for its impressive Renaissance frescoes and beautiful setting.
- Transfer Time: 1hr + 1hr
- Distance: 6km/3.7 miles
- Duration: 2-3hrs approx.
- Ascent: 100m+/328ft+
- Terrain: A mixture of quiet country lanes, gravel tracks and rural paths, with gentle undulations. Expect some uneven and unpaved sections as the trail passes through the open landscapes of the Crete Senesi, with a few gentle climbs and descents along the way.
- Breakfast included

Day Seven: At Leisure
After breakfast at the hotel, enjoy another free day exploring San Gimignano. Visit the impressive Duomo and climb Torre Grossa for panoramic views across the Tuscan countryside, or simply relax over a leisurely lunch, sample the local Vernaccia wine and enjoy a gelato in one of the town’s beautiful piazzas.
- Breakfast & dinner included

Day Eight: “Arrivederci”
Today we check-out of our hotel and say goodbye before transferring back to Pisa airport for our flight home.
- Breakfast included
Accommodations
Dates & Prices
Essential Information
Complimentary group airport transfers are included on arrival and departure days within specific time windows. If your flight falls outside these times, or if you prefer a private airport transfer, these are available for an additional fee. Our team can advise you of the departure times for the group shuttle. To learn more about flight options, payments, and transfers, click here.
Whether you'd like us to arrange your flights or prefer to book your own, we're here to make the process easy. Our team can secure flights from the location that suits you best, or provide all the arrival and departure details you'll need if booking independently.
Shortly before your holiday, you will be invited to join an optional WhatsApp group to connect with your fellow travellers and your Tour Leader.
It is important that you have the correct footwear. It is essential to wear walking boots that are comfortable and preferably lightweight, with some ankle support and a good grip. If you already have a pair of boots that you are happy walking in (including during hot/wet weather and on hard ground), then bring these along. However, if you are bringing new footwear, do make sure they are well broken in before you arrive. The weather, even in summer, can be unpredictable. We would therefore recommend you travel with clothing suitable for all conditions, and suggest you use the following checklist as a guideline of what to take:
- Walking boots with good ankle support
- Waterproofs – jacket and trousers
- Walking poles – recommended as they provide good support for the knees, particularly on downhill sections of walks and when conditions are wet/slippery
- Lightweight trousers and shorts with pockets
- Shirts or t-shirts for walking in
- Walking socks – several pairs
- Lightweight fleece or jumper
- Hat & gloves
- Daysack/rucksack for walking
- Umbrella – it can be used also for protection from the sun as well as rain
- Lightweight drinking bottle to carry water whilst walking
- Small first aid kit – plasters, insect repellant, etc
- Good, high factor sunscreen, sunhat and sunglasses – the sun’s strength is often multiplied in mountainous areas.
Guided walks are included as part of this trip. Your dedicated walking guide will brief you in resort on the daily walking programme.
The walking programme is graded by difficulty, and you can expect to walk varying distances with a range of ascents and descents. Some walks may be challenging, with uneven or rough terrain underfoot and sections at higher altitude. Please refer to the day-by-day itinerary for full details of each walk.
A good level of physical fitness is required to fully enjoy this trip.
It is important that you consider whether your chosen trip is suitable for your level of fitness, mobility and any medical conditions or additional needs. If you are unsure, please contact our team before booking. We will be happy to discuss the trip requirements and your individual circumstances to help you decide whether the trip is suitable for you.
We are committed to treating all customers fairly and will consider any reasonable adjustments where possible. Please let us know before booking if you have a disability, medical condition or any additional requirements that may affect your trip. This allows us to assess whether we can safely and appropriately accommodate your needs and to ensure you have the best possible trip experience.
Care should be taken at all times, particularly on uneven or wet terrain. If you normally use walking poles, we recommend bringing them with you. Sturdy walking boots or walking shoes are essential.
Please note that the route and content of the walking programme may need to change during the trip, at the discretion of the specialist walking guide or local organiser, if local conditions require.
If you have any concerns during your trip, please speak to your specialist walking guide or Solos Tour Leader.
For further information, please refer to our website Terms and Conditions
We recommend that you check passport and visa requirements for the country you are visiting at the State Department if you have a U.S. Passport. Most countries require that your passport have at least six months validity when traveling internationally, and many require that you have one to two blank visa pages for either an entry stamp or visa. As a general rule, please check that your passport has six months validity beyond your planned trip, and if not, please renew your passport with plenty of time to provide Solos with your updated passport information by the final payment due date.
Not sure what travel documents you need? Our trusted partner, sherpa°, makes it easy to check visa and entry requirements based on your destination and passport. One quick check now means smooth sailing later. Click here to learn more.
Voltage 230v
Travel adaptor type C (EuroPlug)




















